New fuchsine

New fuchsine is an organic compound with the formula [(H2N(CH3)C6H3)3C]Cl. It is a green-colored solid that is used as a dye of the triarylmethane class. It is one of the four components of basic fuchsine, and one of the two that are available as single dyes.[1] The other is pararosaniline. It is prepared by condensation of ortho-toluidine with formaldehyde. This process initially gives the benzhydrol 4,4'-bis(dimethylamino)benzhydrol, which is further condensed to give the leuco (colorless) tertiary alcohol [(H2N(CH3)C6H3)3COH, which is oxidized in acid to give the dye.[2]

New fuchsine
Names
Other names
New fuchsin; Magenta III; Basic Violet 2; C.I. 42520
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.019.847
EC Number
  • 221-831-7
UNII
Properties
C22H24ClN3
Molar mass 365.91 g·mol−1
Appearance violet powder
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H315, H318, H319, H335, H350, H351, H373, H400, H410
P201, P202, P260, P261, P264, P271, P273, P280, P281, P302+352, P304+340, P305+351+338, P308+313, P310, P312, P314, P321, P332+313, P337+313, P362, P391, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Use as dye and stain

New fuchsine is used to dye polyacrylonitrile, paper, and leather. In biology, it can be used for staining acid-fast organisms, e.g. by Ziehl-Neelsen stain, and for making Schiff's reagent. As a primary amine, the dye can be diazotized in the laboratory, and the resulting diazonium salt used as a trapping agent in enzyme histochemistry.[3]

Etymology

The name fuchsine recognizes Leonhardt Fuchs.

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See also

References
  1. Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
  2. Thetford, Dean; Updated By Staff (2013). "Triphenylmethane and Related Dyes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2018091620080520.a01.pub2. ISBN 978-0471238966.
  3. Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.
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